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Naphthalimide derivative and application thereof as enzyme inhibitor and pesticide

A technology of naphthalimide and derivatives is applied in the directions of insecticides, biocides, animal repellents, etc., and achieves the effects of good application prospects, simple synthesis and low cost

Inactive Publication Date: 2014-03-19
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the reported naphthalimide derivatives are effective against human N-acetylhexosaminidase, but not against insect chitinase and N-acetylhexosaminidase

Method used

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  • Naphthalimide derivative and application thereof as enzyme inhibitor and pesticide
  • Naphthalimide derivative and application thereof as enzyme inhibitor and pesticide
  • Naphthalimide derivative and application thereof as enzyme inhibitor and pesticide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] 2-(2-(((5-Methyl-1,3,4-thiadiazol-2-yl)methyl)amino)ethyl)-1H-benzo[de]isoquinoline-1,3 Synthesis of (2H)-diketone (1)

[0025]

[0026] Potassium carbonate (383 mg, 2.77 mmol) was added to 2-(2-aminoethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione (500 mg, 2.08 mmol) and 2-chloro A solution of methyl-5-methyl-1,3,4-thiadiazole (206 mg, 1.39 mmol) in 20 mL of acetonitrile was heated under reflux and stirred until the reaction of the starting materials was completed by TLC monitoring, about 12 hours. The reaction solution was suction filtered to remove insoluble matter. The filtrate was evaporated to dryness under reduced pressure, and the residue was separated by silica gel column chromatography (CH 2 Cl 2 / CH 3 OH (30:1)) to give a white solid (250 mg, 0.71 mmol, 51%).

[0027] 1 H NMR (400MHz, CDCl 3 ):δ=8.59(d,J=7.2Hz,2H),8.23(d,J=8.0Hz,2H),7.76(dd,J=8.0,7.2Hz,2H),4.37(t,J=6.0Hz ,2H),4.22(s,2H),3.10(t,J=6.0Hz,2H),2.63(s,3H),1.96ppm(br,1H); 13 C NMR (100MHz, ...

Embodiment 2

[0029] 2-(2-(((5-Methyl-1,3,4-oxadiazol-2-yl)methyl)amino)ethyl)-1H-benzo[de]isoquinoline-1,3 Synthesis of (2H)-diketone (2)

[0030]

[0031] Except replacing 2-chloromethyl-5-methyl-1,3,4-thiadiazole in Example 1 with 2-chloromethyl-5-methyl-1,3,4-oxadiazole, Other conditions and steps were the same as in Example 1 to obtain compound 2 as a white solid with a yield of 50%.

[0032] 1 H NMR (400MHz, CDCl 3 ):δ=8.59(d,J=7.2Hz,2H),8.23(d,J=8.0Hz,2H),7.76(dd,J=8.0,7.2Hz,2H),4.37(t,J=6.0Hz ,2H),4.05(s,2H),3.10(t,J=6.0Hz,2H),2.47(s,3H),1.96ppm(br,1H); 13 C NMR (100MHz, CDCl 3 ): δ=172.0, 165.4, 164.1, 134.1, 131.6, 131.3, 128.2, 127.0, 122.5, 47.1, 43.4, 39.5, 11.0ppm; HRMS-ESI(m / z): Calculated value C 18 H 17 N 4 O 3 [M+H] + , 337.1301; experimental value, 337.1300.

Embodiment 3

[0034] 6-(Dimethylamino)-2-(2-(((5-methyl-1,3,4-thiadiazol-2-yl)methyl)amino)ethyl)-1H-benzo[ Synthesis of de]isoquinoline-1,3(2H)-dione (3)

[0035]

[0036] Divide by 2-(2-aminoethyl)-6-(dimethylamino)-1H-benzo[de]isoquinoline-1,3(2H)-dione to replace Except for 2-aminoethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione, other conditions and steps were the same as in Example 1 to obtain compound 3, yellow oil, yield 50 %.

[0037] 1 H NMR (400MHz, CDCl 3 ):δ=8.54(dd,J=7.2,0.8Hz,1H),8.47-8.40(m,2H),7.64(dd,J=8.4,7.2Hz,1H),7.10(d,J=8.4Hz, 1H), 4.33(t, J=6.4Hz, 2H), 4.21(s, 2H), 3.10(s, 6H), 3.07(t, J=6.4Hz, 2H), 2.62(s, J=3H), 2.16ppm(br,1H); 13 C NMR (100MHz, CDCl 3):δ=172.1,165.6,164.8,164.2,157.0,132.7,131.3,131.1,130.3,125.2,124.8,122.9,114.7,113.2,47.8,47.3,44.7,39.4,15.5ppm;HRMS-ESI(m / z ): Calculated value, C 20 H 22 N 5 O 2 S[M+H] + , 396.1494; experimental value, 396.1494.

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Abstract

The invention provides a naphthalimide derivative and application thereof as enzyme inhibitor and pesticide, and the invention belongs to the field of chemical biology and agricultural insect control technology. In the formula of naphthalimide derivative, R1 is hydrogen, C1-C4 is alkoxy, C1-C4 is alkyl substituted amino or halogen; R2 is hydrogen, C1-C4 is alkyl, C1-C4 is alkoxy substituted phenyl or halogen substituted phenyl; X, Y and Z respectively and independently selected from one of O, S, N and C, which are identical or different; n is 0 or 1. The compound can be used as insect chitinase and n-acetyl hexosamine enzyme inhibitor and pesticide. The invention provides a non-glycosyl novel naphthalimide derivative, which can be used as insect n-acetyl hexosamine enzyme selective inhibitor and pesticide, and has the advantages of simple synthetic method, low cost and good application prospect.

Description

technical field [0001] The invention belongs to the technical field of chemical biology and agricultural pest control, and relates to a naphthalimide derivative and its use as an inhibitor of insect chitinase and N-acetylhexosaminidase and an insecticide. Background technique [0002] At present, most glycosyl hydrolase inhibitors are based on the parent structure of glycosyl, which has the problems of complex synthesis process and high cost. [0003] In 2006, the research group of Dr. Mahuran of the Canadian Children's Hospital discovered a non-glycosyl structure compound - binaphthalimide M31850, which is a human N-acetylhexosaminidase inhibitor (Chem.Biol. , 14, 153-164), whose structure is as follows: [0004] [0005] In 2012, the inventors synthesized a series of derivatives of M31850 and their use as human N-acetylhexosaminidase inhibitors, and applied for a national invention patent, the publication number is CN102911117A, and its general structural formula is as...

Claims

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Application Information

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IPC IPC(8): C07D417/12C07D413/12A01P7/04
CPCA01N43/78A01N43/82C07D413/12C07D417/12
Inventor 杨青刘田钱旭红郭朋
Owner DALIAN UNIV OF TECH
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